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Lipid Hydroperoxide Activation of N-Hydroxy-N-acetylaminofluorene via a Free Radical Route¹

Oklahoma Medical Research Foundation, Biomembrane Research Laboratory, Oklahoma City, Oklahoma 73104

The data presented here demonstrate that linoleic acid hydroperoxide in the presence of methemoglobin or hematin activated the carcinogen N-hydroxy-N-acetyl-2-aminofluorene via the nitroxyl free radical intermediate into 2-nitrosofluorene and N-acetyl-N-acetyl-2-aminofluorene. Ascorbate inhibited the activation, in which case the free radical intermediate was replaced by the ascorbate free radical. On the basis of optical kinetics, we have established that the rate of linoleic acid hydroperoxide decrease paralleled the rate of N-hydroxy-N-acetyl-2-aminofluorene decrease and also the rate of 2-nitrosofluorene increase. The stoichiometry of the reaction was such that, for every 2 linoleic acid hydroperoxide molecules consumed, 2 N-hydroxy-N-acetyl-2-aminofluorene molecules were oxidized and 1 2-nitrosofluorene and 1 N-acetoxy-N-acetyl-2 aminofluorene molecule was formed.

¹ This research was in part supported by Grant 1-RO1-CA18591-01 from the National Cancer Institute.

² To whom requests for reprints should be addressed, at the Oklahoma Medical Research Foundation, Biomembrane Research Laboratory, 825 Northeast 13 Street, Oklahoma City, Okla. 73104.

Received 12/ 9/75. Accepted 4/12/76.